Diisopropylethylamine → HCID 66673582, compound

HRID 423683Notes

Reaction equation

HRID 423683 reaction equation
CN(C(ON1N=[N:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH3:32][CH:33]([O:35][C:36]([N:38]1[CH2:43][CH2:42][CH:41]([C:44]([OH:46])=O)[CH2:40][CH2:39]1)=[O:37])[CH3:34].[Br:47]C1N=CC(N)=CC=1>CN(C=O)C>[Br:47][C:14]1[CH:15]=[CH:10][C:11]([NH:16][C:44]([CH:41]2[CH2:42][CH2:43][N:38]([C:36]([O:35][CH:33]([CH3:34])[CH3:32])=[O:37])[CH2:39][CH2:40]2)=[O:46])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6428116-Bromopyridin-3-amineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 61800653HCID 61800653, compound

Product 1

HCID 66673582HCID 66673582, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Methylethyl 4-{[(4-bromophenyl)amino]carbonyl}-1-piperidinecarboxylate (1.86 g, 54%) was prepared as a white solid from TBTU (4.48 g, 13.95 mmol), diisopropylethylamine (2.43 mL, 13.95 mmol), 1-{[(1-methylethyl)oxy]carbonyl}-4-piperidinecarboxylic acid (2 g, 9.3 mmol), DMF (25 mL) and 6-bromo-3-pyridinamine (1.77 g, 10.23 mmol) in a manner similar to Example 172, Step 1. 1H NMR (400 MHz, CDCl3): δ 8.32 (d, 1H, J=2.7 Hz), 8.07 (dd, 1H, Ja=8.7 Hz, Jb=2.7 Hz), 7.42 (d, 1H, J=8.7 Hz), 7.37 (bs, 1H), 4.90 (septet, 1H, J=6.3 Hz), 4.21 (dd, 2H, Ja=2.4 Hz, Jb=1.4 Hz), 2.87-2.73 (m, 2H), 2.47-2.35 (m, 1H), 1.89 (d, 2H, J=11.9 Hz), 1.80-1.66 (m, 2H), 1.22 (d, 6H, J=6.2 Hz); LRMS (ESI), m/z 370/372 (M+H).

Sources & evidence

ORD record
ord-53859bf0f3424b4596160bcd56664976
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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